CH632754A5 - Process for preparing 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid - Google Patents

Process for preparing 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid Download PDF

Info

Publication number: CH632754A5
Authority: CH; Switzerland
Prior art keywords: dichloro; acid; mixture; ethyl; thenoyl
Prior art date: 1976-09-21

Application number

CH1151177A

Other languages

German (de)

English (en)

Inventor

Jacqueline Suzanne Laforest

Original Assignee

Rolland Sa A

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-09-21

Filing date

1977-09-20

Publication date

1982-10-29

1977-09-20 Application filed by Rolland Sa A filed Critical Rolland Sa A

1982-10-29 Publication of CH632754A5 publication Critical patent/CH632754A5/de

Links

AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 8
MWQVQEFJAIFHFZ-UHFFFAOYSA-N 2,3-dichloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1Cl MWQVQEFJAIFHFZ-UHFFFAOYSA-N 0.000 claims description 7
RHNDEZPJQWPQJU-UHFFFAOYSA-N 4-(carboxymethoxy)-2,3-dichlorobenzoic acid Chemical compound OC(=O)COC1=CC=C(C(O)=O)C(Cl)=C1Cl RHNDEZPJQWPQJU-UHFFFAOYSA-N 0.000 claims description 7
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 7
229930192474 thiophene Natural products 0.000 claims description 6
125000004494 ethyl ester group Chemical group 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
-1 alkyl radical Chemical class 0.000 claims description 4
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
239000012024 dehydrating agents‎ Substances 0.000 claims description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000203 mixture Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IEHZIDHHFQQRLI-UHFFFAOYSA-N 1-(2,3-dichloro-4-hydroxyphenyl)-2-pyridin-1-ium-1-ylethanone;chloride Chemical compound [Cl-].ClC1=C(Cl)C(O)=CC=C1C(=O)C[N+]1=CC=CC=C1 IEHZIDHHFQQRLI-UHFFFAOYSA-N 0.000 description 1
RBJIGQRZLITQJG-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(Cl)=C1Cl RBJIGQRZLITQJG-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JYBASOYAJOAATF-UHFFFAOYSA-N 2-chloro-1-(2,3-dichloro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CCl)C(Cl)=C1Cl JYBASOYAJOAATF-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000012907 medicinal substance Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Hematology (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH1151177A 1976-09-21 1977-09-20 Process for preparing 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid CH632754A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7628274A FR2364916A1 (fr)	1976-09-21	1976-09-21	Procede d'obtention de l'acide dichloro-2,3 (thenoyl-2)-4 phenoxyacetique

Publications (1)

Publication Number	Publication Date
CH632754A5 true CH632754A5 (en)	1982-10-29

Family

ID=9177881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1151177A CH632754A5 (en)	1976-09-21	1977-09-20	Process for preparing 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid

Country Status (21)

Country	Link
JP (1)	JPS5340758A (cs)
BE (1)	BE858848A (cs)
CA (1)	CA1092132A (cs)
CH (1)	CH632754A5 (cs)
CS (1)	CS194693B2 (cs)
DD (1)	DD132870A5 (cs)
DE (1)	DE2742126A1 (cs)
ES (1)	ES462472A1 (cs)
FR (1)	FR2364916A1 (cs)
GB (2)	GB1568319A (cs)
GR (1)	GR63570B (cs)
HU (1)	HU172875B (cs)
IE (1)	IE45967B1 (cs)
IL (1)	IL52881A (cs)
IT (1)	IT1086083B (cs)
NL (1)	NL7710353A (cs)
PL (1)	PL200937A1 (cs)
PT (1)	PT67035B (cs)
RO (1)	RO72173A (cs)
SU (1)	SU736871A3 (cs)
YU (1)	YU222077A (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2916980C2 (de) *	1979-04-26	1981-06-19	Ludwig Heumann & Co GmbH, 8500 Nürnberg	Verfahren zur Herstellung von Thenoyl-phenoxyessigsäureestern

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2458520A (en) *	1945-11-08	1949-01-11	Socony Vacuum Oil Co Inc	Acylation of thiophene

1976
- 1976-09-21 FR FR7628274A patent/FR2364916A1/fr active Granted
1977
- 1977-09-01 CA CA286,003A patent/CA1092132A/en not_active Expired
- 1977-09-02 IL IL52881A patent/IL52881A/xx unknown
- 1977-09-07 IT IT27349/77A patent/IT1086083B/it active
- 1977-09-14 GB GB38258/77A patent/GB1568319A/en not_active Expired
- 1977-09-14 GB GB20299/79A patent/GB1568320A/en not_active Expired
- 1977-09-14 CS CS775985A patent/CS194693B2/cs unknown
- 1977-09-15 PT PT67035A patent/PT67035B/pt unknown
- 1977-09-17 RO RO7791606A patent/RO72173A/ro unknown
- 1977-09-19 GR GR54374A patent/GR63570B/el unknown
- 1977-09-19 DE DE19772742126 patent/DE2742126A1/de not_active Withdrawn
- 1977-09-19 BE BE181030A patent/BE858848A/xx not_active IP Right Cessation
- 1977-09-19 PL PL20093777A patent/PL200937A1/xx unknown
- 1977-09-20 YU YU02220/77A patent/YU222077A/xx unknown
- 1977-09-20 HU HU77RO00000945A patent/HU172875B/hu unknown
- 1977-09-20 ES ES462472A patent/ES462472A1/es not_active Expired
- 1977-09-20 CH CH1151177A patent/CH632754A5/de not_active IP Right Cessation
- 1977-09-20 DD DD7700201120A patent/DD132870A5/xx unknown
- 1977-09-20 JP JP11390077A patent/JPS5340758A/ja active Pending
- 1977-09-21 NL NL7710353A patent/NL7710353A/xx not_active Application Discontinuation
- 1977-09-21 IE IE1933/77A patent/IE45967B1/en unknown
- 1977-09-21 SU SU772524498A patent/SU736871A3/ru active

Also Published As

Publication number	Publication date
GB1568320A (en)	1980-05-29
PT67035A (en)	1977-10-01
ES462472A1 (es)	1978-07-16
PL200937A1 (pl)	1978-05-22
FR2364916B1 (cs)	1979-08-17
SU736871A3 (ru)	1980-05-25
CA1092132A (en)	1980-12-23
CS194693B2 (en)	1979-12-31
PT67035B (en)	1979-02-15
FR2364916A1 (fr)	1978-04-14
IE45967L (en)	1978-03-21
IE45967B1 (en)	1983-01-12
JPS5340758A (en)	1978-04-13
GR63570B (en)	1979-11-20
DE2742126A1 (de)	1978-08-03
RO72173A (ro)	1981-06-26
DD132870A5 (de)	1978-11-15
HU172875B (hu)	1978-12-28
BE858848A (fr)	1978-03-20
IL52881A0 (en)	1977-11-30
YU222077A (en)	1983-02-28
NL7710353A (nl)	1978-03-23
IL52881A (en)	1981-05-20
IT1086083B (it)	1985-05-28
GB1568319A (en)	1980-05-29

Legal Events

Date	Code	Title	Description
1991-05-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2660606C2 (de)	1984-08-02	Verfahren zur Herstellung von Phenylacrylsäureestern, Phenyloxaloacetat-Enolatsalze
DE3852107T2 (de)	1995-03-30	Bestimmte 3-substituierte 2-alkyl-benzofuran-derivate.
US2734904A (en)	1956-02-14	Xcxnhxc-nh
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DE2224655A1 (de)	1972-12-07	Tricyclische Verbindungen und Verfahren zu deren Herstellung
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